Downtown San Francisco during the work week is always swarming with millennials in clothing styles meant to convey ‘simple, smart and purposeful’ yet for many, dating life is proving to be anything but that. The millennial clients that I coach through professional and personal life goals came of age in a time when digital technology had already changed how people communicate, disrupting social rules of dating among other mainstays of modern society. Thirty-nine percent of Millennials admit to interacting more with their phones than the actual people in their lives, making them even less likely to to talk to strangers without clear cause in their everyday comings and goings. Many millennial men who’ve achieved professional success are now ready to marry, but are realizing the strategies they used to find casual sex partners aren’t cutting it for finding ‘the one‘. With no time to sift through dating profiles or spend nights in bars, these guys are engaging coaching to develop proactive dating strategies that set them up for success in their daily activities.

“I want to meet a really smart woman, much smarter than me! Someone who is passionate about pursuing her goals, driven by values that we both share. I want to be attracted to her mind more than anything! But she should want to be healthy and fit and enjoy being sexually active for us to be truly compatible. Financial independence is important too, since living here is so expensive. Is that too much to ask?”

That’s Silicon Valley in a nutshell, and honestly that’s not even a tall order compared to what my high-achieving female clients have on their marital check-list. So while online dating has been effective for solving most people’s casual sex needs, it feels agonizingly inefficient to most people ready to meet someone marriage-worthy, especially with personal brand consciousness and FOMO influencing millennials’ major life decision-making process. I encourage my single clients to attend curated social events or engage in recreational activities with a male/female ratio that benefits them, increasing the odds they meet people of similar caliber who share mutual interests. I ask them to take the approach“if I had to solve this problem in the next two weeks, how would I do it? What can I do to get started today?” which gives people a sense of urgency and gets them ready to apply practical solutions in the here and now.

After mapping out a few actionable plans with a male client, he earnestly asked “is it ever ok to just approach a woman in public these days? You know without coming across as desperate or creepy.” Admittedly I was taken aback by this question – I was struck by the difficult task of overcoming social anxiety they’ve spent less time addressing thanks to technology, while leveraging enough social finesse to engage others in a respectful and compelling way. Many millennial aged men understandably prefer to play it safe in unclear circumstances, or risk coming across like a cheesy pick-up artist (PUA). Have millennials come to rely exclusively on dating apps, social introductions, singles bars and events that serve the function of bars to form romantic connections? Has the heterosexual male to female ‘cold call’ approach become totally obsolete? Like the evolutionary equivalent of the human appendix, wisdom teeth or tonsils, once useful in our dark past but at best should remain dormant or at worst may trigger pain and suffering?

Once upon a time men were far more likely to approach women in public outside of well-defined social circumstances, when our society was more deeply rooted in the notion that ‘masculine persistence wins the heart.’ American media largely produced by men has been dominated by storylines that convey if a woman responds to a man’s advances with disinterest, she can be persuaded to change her mind through a combination of charm, wit, and low-key psychological warfare. This dynamic calls for female passivity, contributing to how women are treated as ‘fair game for romantic pursuits’ in public spaces. The time of reckoning for gender inequality has come with the #metoo movement, an activist-led eruption of female empowerment that has become a global phenomenon, upending the longstanding tolerance of objectification and abuse of women for the purpose of male sexual gratification. Though gender equality across all realms has a long way to go, it is still possible for men to safely and respectfully engage women in public by learning to read social cues with greater sensitivity. It will likely not be easy or feel comfortable. As I said to my male client “approaching a woman in public is graduate-school level game– we’re working on social skill mastery at the kindergarten level- first things first.” (My clients are sturdy and know I don’t dish out what I know they can’t take!)

If you want to approach a woman in public but are unsure of how to proceed, take the time to read the situation closely. This may take time you don’t want to spare- but keep in mind, a rushed approach increases the chance of a failed mission.

HOW TO’S:

Make sure this woman is not wearing a wedding ring. This is an easily avoidable rookie mistake! Practice discreetly checking out left hands in various situations so you can be ready to quickly assess when it matters.

Respect women’s time. Does it look like the woman is in a perceptible hurry? Is she engaged in an activity that she’d probably prefer not to have interrupted? If she’s busy working on a laptop she probably won’t welcome small talk- wait until it’s obvious she’s taking a break to speak to her. Is the woman clearly relaxing, enjoying a meal by herself or having some personal downtime? If she responds with only a fleeting or absent smile, minimal verbal response or eye contact, take the hint and keep it moving. Persistence in the face of a minimal response is only going to feel uncomfortable and annoying to her.

Pay attention to eye contact. Has the woman made purposeful, positive eye contact with you at least a few times? Catching a woman’s eye once might be accidental, twice might be her checking to see if you are still looking at her. Women naturally check their surroundings for their own safety, and women find they need to keep an eye out for guys who might be staring, stalker style. Your job is to make sure you come across as friendly and safe– if you’re so nervous you can’t smile in the split second you catch a woman’s eye, you might not be ready to approach a woman in this manner. Practice talking to women you don’t know in social settings where people are clearly expected to mingle so you develop a sense of how to accurately read non-verbal cues.

Drop the idea that channeling alpha male confidence will lead to a positive outcome. Guys are really attached to the idea that exuding cool confidence is what women want. It’s refreshing and much more likable if you can manage to be yourself and talk with a woman like she’s a person not an object to win over. Better to be awkward and able to laugh at yourself if the situation calls for it! Take it from a woman- we’re often just as concerned with first impressions, and you’ll make it much easier for her to respond to you if open with something genuine and friendly.

Ask her opinion about something related to the shared situation you’re both in, and be sure to listen and show appreciation for her response. This is simple enough to do, especially if she’s in nearby proximity. Respond with something of equal tone, and if possible include an opportunity for her to keep the conversation going.

Get out of your comfort zone, and use light-hearted humor to break the ice. Authentic self-deprecation and self-declared inexperience is an easy way to gain a moment of sympathy from women. Women are natural care-takers, teachers and experts in many, many things! Guys, if you put yourself in a situation where there are women who are excellent at something, you will stand out not only because you’re willing to risk looking foolish, but also because you’re interested in something they clearly enjoy. This only works if you demonstrate a genuine interest in learning. If you keep at it long enough, women will likely take pity on you and offer some support. I’ve seen it happen a million times before!

Adopting these strategies aren’t meant to guarantee that you’ll get a date after perfecting them, but can work to start an engaging conversation that could potentially reveal a reason to stay in touch with a woman as result. Good luck out there, and you’re welcome!

Most accounts of modern dating describe finding lasting love as more elusive than ever. Thanks to mobile dating apps, dating has evolved into a finger-swiping game of ‘matching’ with people whose real intention for long-term dating is nearly impossible to determine. Being an executive and dating coach in the San Francisco Bay Area has given me a front row seat to this phenomenon with an inside view of the good, the bad and the ugly. The highly competitive tech scene here is also known for having an awkward dating culture where both men and women can develop some dumb habits that thwart their long term relationship goals. I feel it’s my duty to share them publicly, air out the gender themes I see, and hopefully shed some light on the issue so more people are successful in their dating endeavors.

My clients are bright, healthy, charismatic people who bemoan their dating struggles as real a ‘pain point’ in their life. In my last article on learned optimism, I outlined the rationale for viewing problems through a positive, solution-focused lens, and how to hold yourself accountable for your role in a problem. When a client tells me “I’d like to meet someone and settle down into a long-term relationship but I’m having a tough time finding them.” I’ll ask “What strategies are you using to meet eligible people? Tell me, what are you currently doing to build a long-term relationship with someone?” This is when the storyline starts to reveal dating habits that can be major roadblocks to developing a lasting romantic relationship.

Dumb dating habit #1: Going on a never-ending cycle of first dates, waiting for that ‘love at first sight’ feeling to signal when it’s time to finally pursue someone for a long term relationship.

First impressions are often not a good predictor of who’ll be a good fit for a long term relationship. In my observation, guys need to take initiative and figure out how to emotionally invest in the process of dating if they want a long term relationship. A lot of men are stuck in a conundrum when they’re looking for a girlfriend- they feel safer with more options, but more options leads to low emotional investment, which leads to a sense of emptiness, which they fill with more creating more options. It’s a vicious circle! Men, start by figuring out what you need to do to care more about the person you’re meeting for a date.

Males are commonly raised to avoid vulnerable emotions, and learn to keep a safe distance from their feelings, especially in matters of the heart. As a result, they can miss out on developing emotional intimacy with someone because they fail to take an active role in building it. In movies, men are portrayed as reluctant participants in intimacy – cinematic stereotypes such as the manic pixie dream girl archetype evolved in order to protect masculine identity in the face of falling in love.

REBOOT: If you don’t work to get inside your feelings and figure out how to genuinely invest in caring about the person sitting across from you, these feelings will not mysteriously emerge on their own. I know you believe you just haven’t met someone who’s attractive enough, smart/accomplished enough, humble and supportive and interested in YOU enough. If this storyline is sounding a lot like you, it’s time to see it for what it is – you’ve got to rise to the occasion and take initiative. Make a real effort to be curious, listen, absorb and relate. Look at it from an economic perspective- wise investments of all kinds pay off big!

Dumb dating habit #2: You’re using dating as a way to compete with your friends- in this game the last one to get off the single train wins.

You’re struggling with choosing someone because you’re too busy rounding out your dating options for more bragging rights with your friends. A proud 20-something year old guy once told me that he and his male roommates had a world map in their house with colored pushpins in it to represent the countries of origin of women they’d each slept with. Why? Because it made them look cool to all their friends, duh! But do you really want to be the last one who still cares about playing this game? It’s like you’re that last guy in your middle school friend group who still cares about who has the most/best Pokémon cards.

Dude at some point, it’s not that crucial anymore! Eventually, most guys want to be with someone that will stand by them when life gets hard, someone to enjoy private moments with, who will honestly be there for them through the thick and thin of their life. Meanwhile, do you want to still be scrolling through your phone contacts looking for someone who actually cares about what happens to you? (besides your family! Not your ex either, she’s probably happily married now with a baby on the way.)

Dumb dating habit # 3: Not noticing when your mind magically fills in the blanks in someone’s potential instead of accepting the current reality as it stands. The problem with this is that your brain gets caught in a vicious cycle of unrealistic expectations. This can lead to feeling mad and resentful when the person falls short of your version of them.

Sometimes women can get ahead of themselves while dating, and lose track of the difference between what is reality and what is wishful thinking. This happens when they fail to notice that someone isn’t demonstrating a consistent investment in getting serious with them. When you fantasize a million steps ahead about how your next dates will play out together it can lead your brain to believing it should and it will, and then when it inevitably doesn’t, you feel shortchanged and frustrated, but keep hoping things will improve. Unrealistic expectations can also lead people to cut things off prematurely which is sabotaging your #relationshipgoals. Confirmation bias is a form of faulty thinking with plenty of scientific evidence supporting people’s propensity to believe something is true because they would like it to be true. Motivated by wishful thinking, individuals will stop gathering information when the evidence gathered so far confirms the views (prejudices) one would like to be true.

REBOOT: DO NOT GET AHEAD OF YOURSELF. If someone isn’t consistently making an effort to set concrete plans with you, showing a genuine interest in connecting with you, stop giving him your mental attention! Be ready to harness some discipline because old habits die hard. You’re perfectly rigorous about keeping your diet paleo, you’re awesome at limiting your drinking to the weekends, but you let your mind go on a wild goose chase over every text thread in your phone! You know you’re in trouble if the guy inside your head is always more fun to think about then the same guy whose text messages rarely extend beyond 3 words and you never quite know where things stand between the two of you. Be honest with yourself. Why would it make sense to want a relationship with someone who’s hot and cold towards you? Inconsistency and unpredictability beget failure in building anything of value. Open your eyes to the people who are making it clear they value you and want to spend time with you.

Dumb dating habit # 4: You over-rely on dating apps and forget that prospective dating partners are everywhere! Your attention is buried in your phone and you never (ever, ever) initiate conversation with a stranger for social purposes.

Pretty much everyone is guilty of digital social isolation these days. You’ve heard this before from those of us who evolved as human beings before the digital era. By limiting yourself to socializing through online/text consumption you are actually limiting yourself to a communication method with WORSE social aptitude results not BETTER. The quality of enjoyment, depth of expression and opportunity to build lasting relationships has evolved over billions of years through face to face communication. Digital communication on the other hand has existed for a fraction of a mili-second and the jury is out if humanity would even survive if we continue to depend on it with today’s enthusiasm. It’s not that I think people shouldn’t enjoy all the latest dating apps, follow each other on social media for entertainment, ease and efficiency, but aim to keep practicing your real life social skills. Every single client who’s taken me up on my encouragement in this area has come back glowing with newfound empowerment and shock, really. Like “I cannot believe I initiated a social conversation with a total stranger (sober, mind you!) AND DIDN’T DIE ON THE SPOT FROM ANGST. I CAN DO ANYTHING NOW!!!” YES! That is the best feeling!

Hollywood’s most iconic bachelor George Clooney (and two time winner of People magazine’s Sexiest Man Alive) is often cited as a ‘success story’ by high achieving, adult men who choose bachelorhood over marriage. Unlike in past decades, society has become far more accepting of men who remain bachelors. Modern day bachelors are frequently financially successful who have adopted an enjoyable lifestyle on their own, dining in singles-scene restaurants or cooking artfully for one, forgoing family style vacations for jaunts to sexually hedonistic cities like Miami, Rio, or Vegas, indulging in expensive and/or time consuming sports like golf, sailing, or tri-athalon training, and of course, finding time to pursue a wide variety of women for company. While a modern day bachelor may dream of the exceptional woman who could excite and inspire him to forgo all of this, in the meantime, there is no shortage of modern, single women willing to gratify his sexual needs, perhaps hoping to be the one to convert him to marital devotion.

Some men feel that a life-long commitment to the same person isn’t right for them. Many people lead rich and fulfilling lives having never married. Staying single is a viable choice for people who feel this way, and absolutely the right choice for those that feel marriage would cause them unhappiness.

A common myth of the modern day bachelor is that none of them have an interest in committed long-term relationships. Some bachelors believe that they want a committed relationship/marriage (‘one day’ as many will explain), and can cite a host of reasons why they continue to be single. The central dilemma for these men often lies in the avoidance of hypocrisy. Meaning, while a stable, intimate relationship has it’s benefits, the desire for sexual variety and freedom is often greater, so these men feel forced to choose. So the question is, why do some men choose bachelorhood over a committed relationship? As Clooney himself has insinuated, relationships are very hard work, and bachelorhood is a strategy to avoid the emotional work necessary for a healthy committed intimate relationship. George Clooney quotes:

“I was in a bar and I said to a friend, `You know, we’ve become those 40-year-old guys we used to look at and say, `isn’t it sad?”

“The holidays are the toughest time for me. I just try to get through them. Being a bachelor has it’s rough spots.”

“We’d get into a fight and I’d just mentally leave. I’d think, ‘In a relationship, we should never have his kind of fight.’ Then, instead of figuring out how to make it work, I looked for a way to get out of it. The truth is, you shouldn’t be married if your that kind of person.”

1. Emotions and relationships aren’t always logical. A healthy marriage requires the ability to experience and manage strong emotions while problem solving. While many men are quite successful at problem-solving and managing conflicts in their work roles and male friendships, they find that intimate relationships do not always follow the same logical path to resolution. These men often develop a disdain for personal relationships that do not feel ‘logical’ because they feel confused and unsuccessful at managing them.

2. Sexual boredom. Some bachelors fear the time when they can no longer confirm their virility through sexual conquests. When a man’s self-esteem is closely tied to accruing new sexual encounters, he is bound to feel a tremendous blow to his ego if he cannot pursue the ’emotional high’ that is often associated with winning a new woman’s affection as evidence that he’s still ‘got it’.

3. Perceived loss of freedom and control. Many bachelors feel they can’t fully be themselves unless they remain unattached to a woman, who they believe will undoubtedly try to control him. Even compromise that is essential to any healthy relationship can feel like a loss of power when a bachelor anticipates a ‘take over’ from the woman he’s dating. Others grow weary of taking on responsibilities for anyone other than themselves (i.e. the old ball and chain.) Bachelors find support for their fears by pointing to married men who have far less time for male-centered activities, and can no longer make financial decisions that only benefit themselves.

4. Avoidance of marital disasters. To estimate his chances of marital success a bachelor often looks to his family and married friends as a prediction of his future. He will often zero in on examples of marital failure- married men who feel compelled to cheat, others who abandoned their children, or married couples who argue and fight over everything. Rather than subject himself to experience these marital disasters with someone he genuinely cares for, he rationalizes that remaining single is a much safer bet.
5. Absence of healthy marriage in childhood. Many bachelors cite an absent father or father-figure in their childhood as a reason for not developing the skills necessary to contribute to a healthy marriage. Others witnessed a father who was repeatedly unfaithful and unhappy in his marital life. These bachelors feel that without a good model to draw from, they are destined to become part of an inevitable, familial chain of marital failure.

6. Difficulty balancing professional goals with marriage. It’s not uncommon for men to wait until they’ve achieved some level of occupational stability and success before choosing to settle down with a partner. Yet some men fear that a marriage and/or family will directly hinder them from making the career strides they envision for themselves (i.e. ‘the workaholic’), and have difficulty accepting that it is possible to have both simultaneously.

7. Misogynistic or devaluing beliefs towards women. A subset of bachelors share an ideology that women are inherently inferior to men, and aren’t worthy of a man’s commitment. Their beliefs prevent them from having enough respect for women to engage in a loving, committed relationship. They might view all women as opportunistic “gold diggers” who are incapable of contributing meaningfully to a man’s life. The origins of their disrespect may come from dysfunctional relationships from their upbringing, who they may have experienced as negligent, unloving, overly dependent on others, or otherwise poor caregivers.

Can bachelors like George Clooney be reformed? (women around the world are holding their breath as they read below)

Many bachelors will wait to until they’re old, bald, and/or grey and in need of a nurse before considering giving up their bachelorhood status- typically when the benefits of bachelorhood are no longer in reach (unless they’re the Hugh Hefner sort, and can buy a young woman’s company). Others will choose to bite the bullet and do it earlier so that they’re not constantly mistaken for their girlfriend’s grandfather.

However there IS hope! Seeking a well-suited professional (mental health professional, religious leader, dating coach) depending on the needs and health of the man, may help them overcome their commitment fears of marriage. Getting professional support can help someone gain insights from their family and dating history in order to pinpoint precisely when and how the running dialogue in a man’s mind became “I’m better suited to bachelorhood. I need variety more than intimacy. I’m not cut out for married life.” Cognitive Behavioral Therapy (CBT) is a highly effective clinical road map for treatment, if a healthy, committed relationship is the desired outcome. And when I say commitment, I don’t mean just to a woman/partner, but to himself. A commitment to giving himself the opportunity to experience and receive deep intimacy, trust, acceptance of imperfection of yourself and another person, and most obviously, love.